Comedy · Writing · The pleasure of paying attention
What makes
something funny?
Gary Gulman and Iliza Shlesinger are my two favorite comedians. Looking closely at their work makes me appreciate how much thought, revision and nerve can live inside a laugh.
A person can spend six minutes talking about state abbreviations and make the room wish there were more states.
That is a fairly good argument for taking comedy seriously.
The subject did not arrive carrying its own entertainment value. Someone noticed something, stayed with it, found a way to make us care and arranged the experience so that caring became ridiculous. Then that person had to stand in front of other people and find out whether any of it worked.
Gary Gulman and Iliza Shlesinger are my two favorite comedians because their work rewards both ways of listening. I can enjoy the laugh. I can also enjoy the decisions that made the laugh possible.
Gulman makes me pay attention to a sentence. Shlesinger makes me pay attention to what a person is doing while insisting they are doing something else. Both can build an entire world around a detail that most people would walk past.
My interest here is personal and literary: what I admire in their public work, and what that work helps me understand about writing. These are my interpretations, with interviews and performances linked so you can explore theirs.
Surprise needs somewhere to land
There is no single explanation that accounts for every laugh. A pun, a pratfall, a family story and a perfectly timed look do not make identical demands on an audience. Even the same joke changes with the person telling it and the people listening.
One useful place to begin is the relationship between expectation and recognition.
Give us enough information to anticipate something. Then take us somewhere we did not anticipate, but can understand immediately. The turn should feel surprising without requiring the audience to assemble furniture before the next sentence.
For an original example: “The restaurant’s menu was seasonal. The QR code was permanent.”
The first sentence establishes a familiar promise about food. The second shifts attention to the way we are expected to order it. The connection is close enough to follow, and the small contradiction supplies the turn.
That does not guarantee a laugh. Perhaps the audience likes QR menus. Perhaps the delivery sounds too pleased with itself. Perhaps the line is more satisfying on the page. But there is a comic decision to examine, rather than a general complaint waiting for the word “hilarious” to arrive.
Recognition also goes beyond agreement. I do not have to share a comedian’s experience to recognize embarrassment, overconfidence, longing or the strenuous effort of appearing relaxed. Specificity gives those feelings a place to happen.
The trick is to notice enough that the familiar becomes visible again.
Gary Gulman
The pleasure
of the exact word.
He can make an apparently minor subject feel worth an unreasonable amount of attention.
A tiny administrative problem becomes a world
Gulman’s state-abbreviations set, available through Team Coco, is a wonderful entry point. He presents the subject through an invented documentary about the people charged with reducing state names to two letters. The documentary is part of the joke, not a historical source.1
What I love is the mismatch between the modest task and the narrative importance it acquires. Most of us have accepted those two letters without demanding an origin story. The routine imagines the human effort behind them, giving a piece of ordinary bureaucracy enough dramatic weight to become a predicament.
That is a distinctive act of attention. A smaller version of the idea could stop at “some abbreviations are strange.” Gulman finds a place where characters, language and institutional seriousness can keep generating possibilities.
In James Altucher’s interview about the set, Gulman discusses years of development, including choices as small as the specificity and sound of the documentary’s stated running time. It is a useful reminder that a detail can establish credibility and carry rhythm at once.2
For a writer, that opens an interesting question: does this detail merely decorate the sentence, or does it change the audience’s relationship to the speaker? An exact number can make a narrator seem informed, obsessive, defensive or magnificently concerned with the wrong thing. The information and the personality arrive together.
Precision that still sounds like a person
Gulman’s love of language is especially appealing to me because a conspicuous vocabulary can so easily become an obstacle. You can hear a writer trying to impress you instead of trying to tell you something.
In a 2025 interview with Anthony Cusumano for Third Coast Review, Gulman describes testing words and adjusting when a choice risks sounding too conspicuously written. He also connects his vocabulary to reading. That combination matters: curiosity supplies possibilities; performance helps select among them.3
A word has a social life as well as a definition. It can sound officious, old-fashioned, overqualified or unexpectedly tender. The funny choice may be the word that reveals how this particular narrator thinks, rather than the rarest word available.
I admire that kind of exactness. It gives the listener a person to follow. A joke assembled from interchangeable clever phrases can impress me briefly; a sentence that could only have come from this mind makes me want the next sentence.
There is a person inside the construction
The publisher’s excerpt from Gulman’s memoir, Misfit: Growing Up Awkward in the ’80s, offers another way into his writing. Its kindergarten opening attends to clothing, neighborhood relationships and the comparative importance of children’s possessions.4
What interests me in that opening is how a child’s scale of importance is allowed to govern the scene. The adult writer can shape the language without dismissing what mattered to the child. A small object can hold an enormous amount of envy or hope when the person looking at it is small, too.
That is a useful standard for affectionate comedy: let the person’s concern be real, even when its expression is funny.
His willingness to discuss depression publicly also deserves respect on its own terms. In his essay for the American Foundation for Suicide Prevention, Gulman writes about his experience of recovery and the value he found in another person’s openness.5 I admire the generosity of making difficult experience speakable. I do not want to turn it into a romantic story about suffering being the price of talent.
In that same Third Coast Review conversation, he credits director Mike Bonfiglio’s work on The Great Depresh, including documentary material that could carry information without forcing every part of the story into a joke.3 It is a thoughtful artistic choice, and a generous acknowledgment of collaboration. The person telling the story remains larger than the requirement to keep everyone laughing.
A comedian can give a thought a better sentence.
A comedian can also give it a body.
Iliza Shlesinger
The thought
becomes a character.
Shlesinger’s physical imagination is a major part of what I admire. An attitude can become audible and visible before it has been fully explained.
A change of voice can expose the gap between the person someone hopes to be and the impulse currently making the decisions.
Physical comedy can carry the argument
In Joel Keller’s 2016 TV Insider interview, Shlesinger describes her physicality as a way of communicating an idea intensely and points to cartoons among her influences. In the same conversation, she explains wanting her material about women to convey understanding alongside the jokes.6
I find those two ideas illuminating together. A character voice does more than interrupt ordinary speech. It can let an audience hear a motive: the appetite beneath the manners, the alarm beneath the confidence, the sales pitch someone is making to themselves.
Shlesinger’s recurring “party goblin,” discussed in that interview, gives an impulse a character rather than leaving it as a general observation about going out.6 My reading of the device is that it makes an internal negotiation easier to recognize. The person knows what a sensible decision would be. Another part of the person has prepared a competing proposal.
There is rich comic territory in that divided self. We can recognize a ridiculous impulse without having to claim that it is our entire identity. Giving the impulse a voice lets the audience inspect it from a little distance.
For writing, the broader possibility is exciting. A character does not always need a backstory and a new scene. Sometimes a small shift in diction is enough to reveal who has taken over the argument.
Authority is funny when we can see it being assembled
Elder Millennial gives Shlesinger a particularly productive point of view. The title establishes a position between generations, and Netflix’s official “Gather Round” clip introduces the pleasure of someone adopting an advisory role.7
I like the tension in that position. Experience can confer useful perspective while leaving a person astonished that they are now considered experienced. The speaker can deliver advice and make the act of delivering advice part of the entertainment.
This is a reason stage persona matters so much. A sentence changes depending on whether it comes from a reluctant expert, an enthusiastic witness, a person defending a terrible decision or someone certain they are the last functioning adult in the building.
Shlesinger’s appeal, for me, includes that willingness to make a point of view theatrical. The audience gets an attitude to engage with, not just a series of statements to approve.
And the subject matter need not belong to every listener for the performance to invite them in. Someone else’s precise account of a social expectation can be funny, interesting and revealing. Shared attention does not require identical biographies.
The apparent spontaneity has a working life
Shlesinger told KCRW in 2019 that she develops jokes while performing and then works on reproducing the laugh, considering pace, wording and whether a piece should survive. That is a valuable description of how discovery can become repeatable craft.8
It helps explain why I resist treating performance as a coating applied after the writing is finished. A thought found through a voice or movement may not exist in its strongest form until it is performed. The body can be part of composition.
An improvised moment that worked once also poses a demanding problem: what, exactly, made it work? The words? The interruption? The expectation established ten minutes earlier? The comedian’s reaction to what had just happened?
Recovering the useful part requires judgment. Merely repeating the sentence may reproduce none of the conditions that made it funny. Revision can involve finding a new setup that earns the same surprise.
That is the labor I admire beneath Shlesinger’s energy: the effort to make something feel alive while knowing enough about it to deliver it again.
A page lets you reread.
A room keeps moving.
Stand-up places a special demand on clarity. A reader can return to the beginning of a sentence. A live audience has to keep listening while the next one arrives.
This makes sequencing part of the joke. Who is speaking? What do they want? What assumption are we supposed to be making? If those answers arrive late, the audience may understand the punchline just as the comedian begins the next setup.
Timing includes the time required to understand. A pause can let an image form, give a character room to react or hold an expectation just long enough for the turn to work. A pause without a purpose is simply time the audience has to fill.
There is also the laugh itself. Once people respond, the performance has changed. A necessary word delivered into that response can disappear. The next line may need space; a visual reaction may continue the joke while the room is still laughing.
That makes restraint a performance skill. A comedian who trusts the moment can allow it to finish. A writer can do something similar by ending the paragraph before explaining the joke back to the reader.
The same mechanism can produce very different comedy
It would be too easy to label Gulman the writer and Shlesinger the performer. Both write. Both perform. What interests me is where each draws my attention.
With Gulman, I am especially conscious of verbal choices and the patience of an idea being developed. With Shlesinger, I am especially conscious of character, shifts in energy and the possibilities of a thought becoming physical. Those are emphases in my appreciation, not boundaries around their abilities.
Studying either should make a writer more attentive to their own material. Copying the visible mannerisms would miss the more useful question: what form does this particular thought need?
Why being correct is not enough
A complaint can be accurate and remain a complaint.
Restaurants do use awkward ordering systems. People do behave differently when they want to impress someone. Meetings do consume hours that participants would prefer to use elsewhere. Agreement supplies a starting point. The writing still has to do something.
Look for a contradiction, a misplaced priority, a revealing image or a character who interprets the situation in an unexpected way. Decide what the audience should notice and what discovery you are saving for later.
Escalation should develop the idea. If every next sentence is simply louder or more extreme, the writer may run out of road quickly. A change in who holds authority, what the narrator believes or what the situation now requires can be more productive than another enormous adjective.
A callback can also do more than repeat a phrase. Bring an earlier detail into a changed situation, and it may acquire a second meaning. The pleasure comes partly from the audience recognizing something and partly from discovering what it can now do.
These are possibilities, not compulsory steps. An audience should not feel a writer checking off a comedy worksheet behind the curtain.
An original writing exercise
From an observation
to a comic point of view
Here is a small workshop example, written for this essay. It is not material by Gulman or Shlesinger, and it is not an imitation of either.
The observation
We use a lot of technology to order lunch.
That gives us a subject, but very little attitude. What specifically bothers or amuses the speaker? The work required? The loss of human contact? The absurd seriousness of using a device with extraordinary computing power to obtain soup?
Choose one direction. For this example, the narrator feels underqualified for a task that should be simple.
A possible line
I went out for lunch and discovered my phone was the only one qualified to order.
Now the narrator has lost status to an object. The line supplies a relationship we can develop. There is still work to do: the wording could be sharper, and the next line should move the situation somewhere.
Try a shorter version and one follow-up
“My phone ordered lunch. I was there in case it needed a ride.”
Possible follow-up: “I paid, though. Apparently I’m its parent.”
The first revision makes the phone active and gives the narrator a smaller supporting role. The follow-up changes that role again. The premise is still doing work; we have not changed subjects merely to add another joke.
On the page, I would compare the versions for clarity, rhythm and voice. In performance, I would also want to know whether the setup makes the situation understandable without extra explanation. A useful line in an essay may need a different introduction onstage.
The point of the exercise is to generate choices. Sometimes the first version has the best voice. Sometimes a shorter version removes the very hesitation that made the speaker funny. Editing should protect the useful oddness while clearing away what gets in its way.
A revision process that leaves room for discovery
First, say plainly what the observation is. Then write several possible attitudes toward it. Affection, suspicion, embarrassment and unearned confidence can lead to entirely different pieces about the same subject.
Read the draft aloud. Mark where the listener needs information and where the sentence actually turns. Look for words placed after the turn that explain something the reader already understood.
Try a different order. Try a concrete noun where an adjective is doing vague work. Try letting the narrator reveal the problem through a decision instead of announcing a personality trait.
Then seek a response from someone who did not help build the piece. For a written essay, let them read without coaching their interpretation. For stand-up, the material eventually needs the conditions of performance. A friend reassuring you that you are funny cannot answer every question a room will ask.
A weak response is information, but it is incomplete information. The idea may be unclear, familiar, misplaced in the set or wrong for that audience. Resist rewriting everything after one response. Also resist explaining indefinitely why people ought to have laughed.
The person in the joke still matters
What I enjoy most in comedy is the feeling that somebody has looked closely enough to find us recognizable.
Sharpness can coexist with affection. A narrator can expose a foolish decision while allowing the person making it to have a motive beyond being the designated fool. Desire, pride and embarrassment offer more possibilities than a dismissive label.
This does not require making every joke gentle. It asks for enough precision to know what the joke is actually doing. Is it finding a contradiction? Exposing a pretense? Giving a familiar anxiety a ridiculous shape? Or is it relying on the audience’s willingness to dislike somebody?
That distinction matters to me as a writer. I want readers to leave a piece with more curiosity about people, even when the people have behaved in a way that deserves a paragraph.
My separate essay on writing humor books and essay collections explores how that sensibility carries across a longer manuscript. Here, Gulman and Shlesinger offer something more immediate: two distinctive minds making choices in front of an audience.
Spend some time with the work
A few good places to begin
Enjoy these first. If you return to them with a writer’s curiosity, choose one thing to listen for at a time.
- Gary Gulman’s state-abbreviations set
Listen for how a modest subject acquires importance and how the language helps sustain that imagined world. - Gulman on The Set Up with J.P. Buck
The performer and CONAN’s comedy producer discuss the construction of the set. A useful companion to the finished performance. - The publisher’s excerpt from Misfit
Read for the child’s point of view and the adult writer’s selection of detail. Notice what gets explained and what is trusted to the reader. - Shlesinger’s official Elder Millennial clip
Listen for the relationship she establishes with her audience, then notice how adopting a role changes the delivery. - Shlesinger’s KCRW interview about developing material
Her account of finding jokes in performance is a useful counterweight to the idea that all writing happens alone at a desk.
I like what a good laugh asks us to notice.
Gulman can make me care about the language surrounding something I had barely considered. Shlesinger can make a private argument feel as though it has walked into the room and introduced itself.
What stays with me is the attention. A thought has been pursued far enough to become particular. A performance has been shaped enough to feel alive. Someone has trusted that a very specific way of seeing might be worth sharing.
That is part of the pleasure I look for in my own humor and personal essays. I want the reader to recognize a person, enjoy a sentence and occasionally have to stop reading because the sentence worked.
And I like knowing that something as unpromising as two letters on an envelope can reward that much care.